Synthesis of 20-nor-salvinorin A

Patent metadata

Field	Value
Publication number	US-11512075-B2
Application number	US-201816622111-A
Country	US
Kind code	B2
Filing date	Jun 7, 2018
Priority date	Jun 14, 2017
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

The invention provides 20-nor-salvinorin A, an analog of the kappa-opioid agonist salvinorin A. The 20-nor-salvinorin A is an active kappa-opioid modulator and can be used for treatment of medical conditions wherein modulation of the kappa-opioid receptor is medically indicated, such as pain, pruritis, depression, or inflammation, or conditions implicating perception and consciousness. 20-nor-salvinorin A can be less additive when used in treatment compared to a mu-opioid receptor agonist, and 20-nor-salvinorin A is more stable in vivo than is parent compound salvinorin A. The invention further provides synthetic intermediates and procedures for preparation of 20-nor-salvinorin A.

First claim

What is claimed is:

1. A compound of formula 20-nor-salvinorinA

2. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable excipient.

3. A method of modulating a kappa-opioid receptor, comprising contacting the kappa-opioid receptor with an effective amount or concentration of a compound of claim 1 .

4. A method of treating a medical condition in a patient, wherein modulation of a kappa-opioid receptor is medically indicated, comprising administering to the patient an effective dose of the compound of claim 1 .

5. The method of claim 4 , wherein the medical condition is selected from pain, pruritis, depression, or inflammation, or conditions implicating perception and consciousness.

6. A method for treatment of a medical condition in a patient, comprising administering to the patient an effective dose of the compound of claim 1 , wherein the medical condition is selected from pain, pruritis, depression, or inflammation, or conditions implicating perception and consciousness.

Assignees

• Scripps Research Inst

Inventors

• Shenvi Ryan
• Roach Jeremy
• Sasano Yusuke
• Bohn Laura
• Schmid Cullen

Classifications

• C07D407/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07C2602/28

  Hydrogenated naphthalenes · CPC title

• A61K31/366

  having six-membered rings, e.g. delta-lactones · CPC title

• C07D307/54

  Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07C2601/14

  The ring being saturated · CPC title